Pyridine → N-(2-Bromophenyl)cinnamamide

HRID 1745908

Reaktionsgleichung

Reaktionsgleichung von HRID 1745908
[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].N1C=CC=CC=1.[CH2:15](Cl)[CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])(O)=[O:26].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:15](=[O:26])[CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 119922-BromoanilineHCID 94242Benzene, (3-chloro-1-propenyl)-HCID 516892Sodium Bicarbonate

Produkt 1

HCID 764332N-(2-Bromophenyl)cinnamamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Bromoaniline (48.41 g, 281.4 mMol) was dissolved in 500 mL of anhydrous DCM under an atmosphere of dry N2. Pyridine (45.5 mL, 563 mMol) was then added and the reaction was subsequently cooled to 0° C. after which time cinnamyl chloride (46.9 g, 281.4 mMol) was added. The reaction mixture was slowly warmed up to ambient temperature and then stirred overnight at ambient temperature. The reaction was diluted with 300 mL of saturated aqueous NaHCO3 and then extracted with DCM. The DCM layer was then washed three times with 10% aqueous NaHSO4 followed by saturated aqueous NaHCO3 and finally brine. The DCM layer was then dried over Na2SO4, filtered and concentrated under vacuum to give 85.08 g of a tan solid as the title compound 61A.

Aufarbeitung

  1. additionwas added
  2. extractionextracted with DCM
  3. washThe DCM layer was then washed three times with 10% aqueous NaHSO4
  4. dry with materialThe DCM layer was then dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f71303a962894eb5b2b69c7a4e1a2188
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07019147B1

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